Dig 20 halogenotriazinyl group-containing fiber reactive dyes, their preparation and their use

Abstract

Compounds of the formula ##STR1## in which the variables are as defined in the claims, which are suitable as fibre-reactive dyes for dyeing or printing widely varying fibre materials are described.

What is claimed is: 
     
       1. A compound of the formula ##STR25## in which B is a bridge member of the formula   --NR.sub.2 --(alk)--NR.sub.3 --                            (2a)     or     --NR.sub.2 --(alk'--O).sub.r --(alk')--NR.sub.2 '--        (2b)     or ##STR26## (R) n  is n identical or different radicals from the group consisting of C 1  -C 4  alkyl, C 1  -C 4  alkoxy, halogen and sulfo and (R') m  is m identical or different radicals from the group consisting of C 1  -C 4  alkyl, C 1  -C 4  alkoxy, halogen and sulfo,   n and m independently of one another are each the number 0, 1 or 2,   R 1 , R 1  ', R 2  and R 2  ' independently of one another are each hydrogen or substituted or unsubstituted C 1  -C 4  alkyl,   R 3  is C 1  -C 6  alkyl which is substituted by hydroxyl,   R 4  is hydrogen or C 1  -C 4  alkyl,   (alk) is straight-chain or branched C 2  -C 12  alkylene and (alk') is straight-chain or branched C 2  -C 4  alkylene,   X 1  and X 2  independently of one another are each halogen, 3-carboxypyridin-1-yl or 3-carbamoylpyridin-1-yl,   Y and Y' independently of one another are each vinyl or a radical --CH 2  --CH 2  --U and U is a leaving group, and   p and q independently of one another are each the number 0 or 1 and   r is the number 1, 2 or 3.   
     
     
       2. A compound according to claim 1, in which (R) n  and (R') m  independently of one another are each 0, 1 or 2 identical or different radicals from the group consisting of methyl, methoxy and sulfo.   
     
     
       3. A compound according to claim 1, in which X 1  and X 2  are identical and are each chlorine or fluorine.   
     
     
       4. A compound according to claim 1, in which R 1  and R 1  ' are identical and are each hydrogen or C 1  -C 4  alkyl.   
     
     
       5. A compound according to claim 1, in which p and q are each the number 1.   
     
     
       6. A compound according to claim 1, in which X 1  and X 2  are identical and are each chlorine,   R 1  and R 1  ' are identical and are each hydrogen, methyl or ethyl,   (R) n  and (R') m  are identical and are each 0, 1 or 2 identical or different radicals from the group consisting of methyl, methoxy and sulfo,   Y and Y' are identical and are each vinyl or β-sulfatoethyl and   p and q are each the number 1.   
     
     
       7. A compound according to claim 1, in which B is a radical of the formulae (2a), (2b) or (2c) defined in claim 1, in which   (alk) is straight-chain or branched C 2  -C 6  alkylene,   (alk') is 1,2-ethylene,   r is the number 2 or 3,   R 2  and R 2  ' are each hydrogen,   R 3  is monohydroxy-substituted C 1  -C 4  alkyl and   R 4  is hydrogen.   
     
     
       8. A compound according to claim 1, in which B is a radical of the formula (2a).   
     
     
       9. A compound according claim 1, in which B is a radical of the formula (2a) defined in claim 1, in which   R 2  is hydrogen,   (alk) is straight-chain or branched C 2  -C 4  alkylene and   R 3  is monohydroxy-substituted C 1  -C 4  alkyl.   
     
     
       10. A compound according to claim 1, of the formula ##STR27## in which X 1  and X 2  are identical and are each chlorine, R 1  and R 1  ' are each hydrogen, (R) n  and (R') m  are identical and are each 0, 1 or 2 identical or different radicals from the group consisting of methyl, methoxy and sulfo,   Y and Y' are identical and are each vinyl or β-sulfatoethyl and   B is a radical of the formula   --NR.sub.2 --(alk)--NR.sub.3 --                            (2a)       in which R 2  is hydrogen,   (alk) is straight-chain or branched C 2  -C 4  alkylene and   R 3  is monohydroxy-substituted C 1  -C 4  alkyl.   
     
     
       11. A compound according to claim 10, in which B is the radical --NH--CH 2  CH 2  --N(CH 2  CH 2  OH)--.   
     
     
       12. A process for the preparation of a compound of the formula (1) according to claim 1, which comprises reacting in each case about 1 molar equivalent of a compound of the formula ##STR28## and   H--B--H                                                    (6),     in which B, (R) n , (R') m , R 1 , R 1  ', X 1 , X 2 , Y, p and q are each as defined above, with one another in any sequence.   
     
     
       13. A process for dyeing or printing fibre material containing hydroxyl groups or containing nitrogen, which process comprises the step of applying to said fibre material a tinctorially effective amount of a compound of the formula (1) according to claim 1. 
     
     
       14. A process according to claim 13, wherein said fibre material is cellulosic fibre material.